(Z)-2,3-Di-chloro-1,4-bis-(4-chloro-phen-yl)but-2-ene-1,4-dione

Area of Science:

• Crystallography
• Organic Chemistry
• Solid-State Chemistry

Background:

• Understanding the solid-state structure of organic compounds is crucial for predicting their physical and chemical properties.
• The presence of multiple halogen atoms and carbonyl groups suggests potential for diverse intermolecular interactions.

Purpose of the Study:

• To elucidate the crystal structure of the title compound (C16H8Cl4O2).
• To analyze the molecular conformation and intermolecular interactions within the crystal lattice.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the crystal structure.
• Analysis of bond lengths, bond angles, and torsion angles provided conformational insights.
• Intermolecular interactions such as halogen bonds, hydrogen bonds, and pi-pi stacking were identified and quantified.

Main Results:

• The compound crystallizes with two independent molecules in the asymmetric unit, both exhibiting Z-conformation around the central double bond.
• Significant differences in C-C-C-O torsion angles were observed between the two independent molecules.
• Short halogen (Cl abbit O, Cl abbit Cl) contacts and C-H abbit Cl, C-H abbit O interactions were identified, leading to chain propagation along the [100] direction.
• Pi-pi stacking interactions between aromatic units were observed with a centroid-centroid distance of 3.9264 (6) Å.

Conclusions:

• The crystal structure is stabilized by a combination of halogen bonding, hydrogen bonding, and pi-pi stacking interactions.
• The observed conformational variations in the independent molecules highlight the flexibility of the organic framework.
• The detailed structural analysis provides a foundation for understanding the material properties and potential applications of this compound.